Open AccessPalladium Hydride Promoted Stereoselective Isomerization of Unactivated Di(exo)methylenes to Endocyclic Dienes
Author(s) -
Michael E. Jung,
Gloria Lee,
Hung Viet Pham,
K. N. Houk
Publication year - 2014
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/ol500710v
Subject(s) - chemistry , isomerization , stereoselectivity , palladium , hydride , organic chemistry , medicinal chemistry , polymer chemistry , catalysis , hydrogen
The exomethylenes of 2,6-disubstituted bicyclo[3.3.1]nonan-9-ones 2 are readily isomerized over a palladium catalyst under an atmosphere of hydrogen to predominantly form the isomer 3 with C2 symmetry with very little formation of the analogous product with C(s) symmetry. A hydrogen source is essential to effect the rearrangement.
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